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Air was really had me going and as well Kimi ga Nozomu Eien and Clannad the movie I really can't pick the most depressing/sadest anime because they all got me pretty heavy.

My question to anyone that reads this is -

" Why do we watch depressing anime if we know it will make us cry and sometimes even depress ourselves just by getting emotionally envolved in the anime itself and its characters"?

My answer is.... I still don't know heh, I'm just drawn in by them some how I crave them as if without them id be lost I love Drama romance and real Tear jerkers inside anime and I like comedy. So their is still no definite answer for why I watch them and like them my only answer is I LIKE THEM.

bokurano's sad, but not in a make you cry way. tis a great series though; the first half is really good and yes, uninstall is really catchy. planet survive had a few sad moments that i thought were nice.

i'd rather watch a good sad anime as it stays with you long after you've watched it; it makes you think about stuff. it emotionally hits you. for something like hayate no gotoku, i may remember the roflmao scenes in episode one and when tama speaks for the first time and the macross 7 parodies, but the rest of it will never stick with me.

bokurano's sad, but not in a make you cry way. tis a great series though; the first half is really good and yes, uninstall is really catchy. planet survive had a few sad moments that i thought were nice.

i'd rather watch a good sad anime as it stays with you long after you've watched it; it makes you think about stuff. it emotionally hits you. for something like hayate no gotoku, i may remember the roflmao scenes in episode one and when tama speaks for the first time and the macross 7 parodies, but the rest of it will never stick with me.

There are a few anime that stays with me for a long time, but you're right, even though Bokurano is sad, you don't really think about it day after day.

And yes, I often think about Kimi ga Nozomu Eien and SaiKano, since those have the most emotional impact on me. Unfortunately, the third candidate for making me think about it a lot would have to be School Days, even though I really want it out of my head instead.

Jungle Emperor Leo Movie- The greatest meaning to one's life in the world.
AIR TV- Epiosde 6, 11 and last
Kanon 2006- Like everyone's stories ^-^ curse you Jun!
Kanon 2002- A classic XD
Clannad- I know what is yet to come...I hope the anime can make it even better
Ojamajo Doremi End >.< no god make more no more pretty cure >.<

Elfen Lied is a really really underlying dirty series....I made it through the whole movie without crying. Right at the end, when we see Lucy's moment with Kouta, we see her more humane side, man that made me feel sorry for her, I was bawling my eyes....Dirty trick....I went from hating Lucy to loving her in 2 minutes, biggest emotional change ever in a series.

The ending of Texhnolyze really teared me up for some reason . I haven't cried watching an anime like this since Grave of the Fireflies.

Spoiler for Texhnolyze's ending:

For some reason Ichise's death is the only one to strike me as emotional, he was the one with the biggest desire to live the entire time probably. I don't know, it just gets me so sad, MOST DEPRESSING END EVER.

A lot of people mentioned SaiKano. I'll just say that I was a manga reader, so I can't really comment on the anime. But, the series, along with the Iriya no Sora OVA and Rumbling Hearts, left me a little sad, but more importantly, they left me with a slightly greater sense of hope.

Saikano, which speaks for itself, really, and that one episode of Cowboy Bebop, with the guy who wanted Spike to teach him how to fight, that really got me. In fact, Cowboy Bebop does that a lot, especially the last episode.